Aluminium lithium hydride → N-(1-(3-(4-Chlorophenyl)-1-hydroxypentan-3-yl)-1H-indol-4-yl)methanesulfonamide
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([CH2:14][CH3:15])[CH2:9][C:10](OC)=[O:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([CH2:14][CH3:15])[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of the product of Step H (60 mg, 0.138 mmol) in THF (5 mL) was added LiAlH4 (10.4 mg, 0.276 mmol) at 0° C. The mixture was stirred for 1 h and quenched with H2O (2 mL), extracted with ethyl acetate, and washed with brine (5 mL), dried over sodium sulfate, then filtered. After removing the organic solvent, the residue was purified by silica gel chromatography (EA/PE=1:3) to afford the title racemic compound. The racemic compound was submitted to chiral SFC separation using AS-H column (50% EtOH/CO2, 4.6×250 mm, 39.3° C.) to give two separated enantiomers. LC/MS m/z=406.9[M+H]+.